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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-06 15:16:49 UTC

Update Date

2022-03-07 02:51:41 UTC

HMDB ID

HMDB0014617

Secondary Accession Numbers

HMDB14617

Metabolite Identification

Common Name

Methohexital

Description

Methohexital is only found in individuals that have used or taken this drug. It is an intravenous anesthetic with a short duration of action that may be used for induction of anesthesia. [PubChem]Methohexital binds at a distinct binding site associated with a Cl^- ionopore at the GABA_A receptor, increasing the duration of time for which the Cl^- ionopore is open. The post-synaptic inhibitory effect of GABA in the thalamus is, therefore, prolonged.

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

HMDB0014617
     RDKit          3D
Methohexital
 37 37  0  0  0  0  0  0  0  0999 V2000
   -2.4762    3.7336   -0.3479 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3956    3.1391   -0.7876 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4782    1.8105   -1.3940 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6611    0.7640   -0.6633 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8066    1.0985   -0.6149 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4116    1.2188   -1.9939 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5124    0.0176    0.0709 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0953   -0.8593    0.6494 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8353   -1.9336    1.3529 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0301   -3.1201    0.4716 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8114   -0.4802   -1.4624 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8178   -0.3617   -2.7121 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9430   -1.7557   -0.8458 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2054   -1.8870    0.5389 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3163   -3.0154    1.0557 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3372   -0.7123    1.3135 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6073   -0.8816    2.7366 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2079    0.5568    0.7077 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5730    1.5689    1.3580 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4475    4.7184    0.1064 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4292    3.2321   -0.4379 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4488    3.6323   -0.7006 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1293    1.8494   -2.4544 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5289    1.4014   -1.3944 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9556    2.0748   -0.0958 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8901    1.9538   -2.6386 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4322    0.1910   -2.4410 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4556    1.6155   -1.8916 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3280   -2.2221    2.2877 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8522   -1.5676    1.6619 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0599   -3.4982    0.5159 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3723   -3.9409    0.8268 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8104   -2.8979   -0.5935 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8339   -2.5857   -1.4779 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5777   -1.4460    2.8231 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7781    0.0846    3.2446 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8441   -1.4956    3.2262 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  5  7  1  0
  7  8  3  0
  8  9  1  0
  9 10  1  0
  4 11  1  0
 11 12  2  0
 11 13  1  0
 13 14  1  0
 14 15  2  0
 14 16  1  0
 16 17  1  0
 16 18  1  0
 18 19  2  0
 18  4  1  0
  1 20  1  0
  1 21  1  0
  2 22  1  0
  3 23  1  0
  3 24  1  0
  5 25  1  0
  6 26  1  0
  6 27  1  0
  6 28  1  0
  9 29  1  0
  9 30  1  0
 10 31  1  0
 10 32  1  0
 10 33  1  0
 13 34  1  0
 17 35  1  0
 17 36  1  0
 17 37  1  0
M  END

474
  Mrv0541 02231214422D          

 19 19  0  0  1  0            999 V2000
    4.7291   -0.5487    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8711   -0.5487    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3001   -3.0238    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0145   -1.7862    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.5856   -1.7862    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.3001   -0.5487    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7126    0.1658    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8876    0.1658    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0145   -0.9612    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5856   -0.9612    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5376    0.1658    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3001   -2.1988    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0625    0.1658    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3001    0.8803    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7291   -2.1988    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500    0.8803    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8876    1.5948    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4751    2.3092    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8876    3.0238    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  9  2  0  0  0  0
  2 10  2  0  0  0  0
  3 12  2  0  0  0  0
  4  9  1  0  0  0  0
  4 12  1  0  0  0  0
  4 15  1  0  0  0  0
  5 10  1  0  0  0  0
  5 12  1  0  0  0  0
  6  7  1  0  0  0  0
  6  8  1  0  0  0  0
  6  9  1  0  0  0  0
  6 10  1  0  0  0  0
  7 11  1  0  0  0  0
  7 14  1  0  0  0  0
  8 13  1  0  0  0  0
 13 16  2  0  0  0  0
 14 17  3  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0014617

> <DATABASE_NAME>
hmdb

> <SMILES>
CCC#CC(C)C1(CC=C)C(=O)NC(=O)N(C)C1=O

> <INCHI_IDENTIFIER>
InChI=1S/C14H18N2O3/c1-5-7-8-10(3)14(9-6-2)11(17)15-13(19)16(4)12(14)18/h6,10H,2,5,9H2,1,3-4H3,(H,15,17,19)

> <INCHI_KEY>
NZXKDOXHBHYTKP-UHFFFAOYSA-N

> <FORMULA>
C14H18N2O3

> <MOLECULAR_WEIGHT>
262.3043

> <EXACT_MASS>
262.131742452

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
27.402358268553048

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
5-(hex-3-yn-2-yl)-1-methyl-5-(prop-2-en-1-yl)-1,3-diazinane-2,4,6-trione

> <ALOGPS_LOGP>
2.43

> <JCHEM_LOGP>
2.286783320666666

> <ALOGPS_LOGS>
-3.70

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.73130483464523

> <JCHEM_POLAR_SURFACE_AREA>
66.48

> <JCHEM_REFRACTIVITY>
71.5071

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.24e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
methohexital

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0014617
     RDKit          3D
Methohexital
 37 37  0  0  0  0  0  0  0  0999 V2000
   -2.4762    3.7336   -0.3479 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3956    3.1391   -0.7876 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4782    1.8105   -1.3940 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6611    0.7640   -0.6633 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8066    1.0985   -0.6149 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4116    1.2188   -1.9939 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5124    0.0176    0.0709 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0953   -0.8593    0.6494 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8353   -1.9336    1.3529 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0301   -3.1201    0.4716 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8114   -0.4802   -1.4624 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8178   -0.3617   -2.7121 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9430   -1.7557   -0.8458 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2054   -1.8870    0.5389 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3163   -3.0154    1.0557 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3372   -0.7123    1.3135 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6073   -0.8816    2.7366 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2079    0.5568    0.7077 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5730    1.5689    1.3580 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4475    4.7184    0.1064 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4292    3.2321   -0.4379 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4488    3.6323   -0.7006 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1293    1.8494   -2.4544 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5289    1.4014   -1.3944 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9556    2.0748   -0.0958 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8901    1.9538   -2.6386 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4322    0.1910   -2.4410 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4556    1.6155   -1.8916 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3280   -2.2221    2.2877 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8522   -1.5676    1.6619 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0599   -3.4982    0.5159 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3723   -3.9409    0.8268 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8104   -2.8979   -0.5935 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8339   -2.5857   -1.4779 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5777   -1.4460    2.8231 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7781    0.0846    3.2446 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8441   -1.4956    3.2262 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  5  7  1  0
  7  8  3  0
  8  9  1  0
  9 10  1  0
  4 11  1  0
 11 12  2  0
 11 13  1  0
 13 14  1  0
 14 15  2  0
 14 16  1  0
 16 17  1  0
 16 18  1  0
 18 19  2  0
 18  4  1  0
  1 20  1  0
  1 21  1  0
  2 22  1  0
  3 23  1  0
  3 24  1  0
  5 25  1  0
  6 26  1  0
  6 27  1  0
  6 28  1  0
  9 29  1  0
  9 30  1  0
 10 31  1  0
 10 32  1  0
 10 33  1  0
 13 34  1  0
 17 35  1  0
 17 36  1  0
 17 37  1  0
M  END

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 474                                               
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  O   UNK     0       8.828  -1.024   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0       3.493  -1.024   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0       6.160  -5.644   0.000  0.00  0.00           O+0
HETATM    4  N   UNK     0       7.494  -3.334   0.000  0.00  0.00           N+0
HETATM    5  N   UNK     0       4.826  -3.334   0.000  0.00  0.00           N+0
HETATM    6  C   UNK     0       6.160  -1.024   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.930   0.309   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       5.390   0.309   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       7.494  -1.794   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.826  -1.794   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       8.470   0.309   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       6.160  -4.104   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       3.850   0.309   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       6.160   1.643   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       8.828  -4.104   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       3.080   1.643   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       5.390   2.977   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       4.620   4.311   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       5.390   5.644   0.000  0.00  0.00           C+0
CONECT    1    9                                                            
CONECT    2   10                                                            
CONECT    3   12                                                            
CONECT    4    9   12   15                                                  
CONECT    5   10   12                                                       
CONECT    6    7    8    9   10                                             
CONECT    7    6   11   14                                                  
CONECT    8    6   13                                                       
CONECT    9    1    4    6                                                  
CONECT   10    2    5    6                                                  
CONECT   11    7                                                            
CONECT   12    3    4    5                                                  
CONECT   13    8   16                                                       
CONECT   14    7   17                                                       
CONECT   15    4                                                            
CONECT   16   13                                                            
CONECT   17   14   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18                                                            
MASTER        0    0    0    0    0    0    0    0   19    0   38    0
END

COMPND    HMDB0014617
HETATM    1  C1  UNL     1      -2.476   3.734  -0.348  1.00  0.00           C  
HETATM    2  C2  UNL     1      -1.396   3.139  -0.788  1.00  0.00           C  
HETATM    3  C3  UNL     1      -1.478   1.811  -1.394  1.00  0.00           C  
HETATM    4  C4  UNL     1      -0.661   0.764  -0.663  1.00  0.00           C  
HETATM    5  C5  UNL     1       0.807   1.098  -0.615  1.00  0.00           C  
HETATM    6  C6  UNL     1       1.412   1.219  -1.994  1.00  0.00           C  
HETATM    7  C7  UNL     1       1.512   0.018   0.071  1.00  0.00           C  
HETATM    8  C8  UNL     1       2.095  -0.859   0.649  1.00  0.00           C  
HETATM    9  C9  UNL     1       2.835  -1.934   1.353  1.00  0.00           C  
HETATM   10  C10 UNL     1       3.030  -3.120   0.472  1.00  0.00           C  
HETATM   11  C11 UNL     1      -0.811  -0.480  -1.462  1.00  0.00           C  
HETATM   12  O1  UNL     1      -0.818  -0.362  -2.712  1.00  0.00           O  
HETATM   13  N1  UNL     1      -0.943  -1.756  -0.846  1.00  0.00           N  
HETATM   14  C12 UNL     1      -1.205  -1.887   0.539  1.00  0.00           C  
HETATM   15  O2  UNL     1      -1.316  -3.015   1.056  1.00  0.00           O  
HETATM   16  N2  UNL     1      -1.337  -0.712   1.313  1.00  0.00           N  
HETATM   17  C13 UNL     1      -1.607  -0.882   2.737  1.00  0.00           C  
HETATM   18  C14 UNL     1      -1.208   0.557   0.708  1.00  0.00           C  
HETATM   19  O3  UNL     1      -1.573   1.569   1.358  1.00  0.00           O  
HETATM   20  H1  UNL     1      -2.448   4.718   0.106  1.00  0.00           H  
HETATM   21  H2  UNL     1      -3.429   3.232  -0.438  1.00  0.00           H  
HETATM   22  H3  UNL     1      -0.449   3.632  -0.701  1.00  0.00           H  
HETATM   23  H4  UNL     1      -1.129   1.849  -2.454  1.00  0.00           H  
HETATM   24  H5  UNL     1      -2.529   1.401  -1.394  1.00  0.00           H  
HETATM   25  H6  UNL     1       0.956   2.075  -0.096  1.00  0.00           H  
HETATM   26  H7  UNL     1       0.890   1.954  -2.639  1.00  0.00           H  
HETATM   27  H8  UNL     1       1.432   0.191  -2.441  1.00  0.00           H  
HETATM   28  H9  UNL     1       2.456   1.616  -1.892  1.00  0.00           H  
HETATM   29  H10 UNL     1       2.328  -2.222   2.288  1.00  0.00           H  
HETATM   30  H11 UNL     1       3.852  -1.568   1.662  1.00  0.00           H  
HETATM   31  H12 UNL     1       4.060  -3.498   0.516  1.00  0.00           H  
HETATM   32  H13 UNL     1       2.372  -3.941   0.827  1.00  0.00           H  
HETATM   33  H14 UNL     1       2.810  -2.898  -0.594  1.00  0.00           H  
HETATM   34  H15 UNL     1      -0.834  -2.586  -1.478  1.00  0.00           H  
HETATM   35  H16 UNL     1      -2.578  -1.446   2.823  1.00  0.00           H  
HETATM   36  H17 UNL     1      -1.778   0.085   3.245  1.00  0.00           H  
HETATM   37  H18 UNL     1      -0.844  -1.496   3.226  1.00  0.00           H  
CONECT    1    2    2   20   21
CONECT    2    3   22
CONECT    3    4   23   24
CONECT    4    5   11   18
CONECT    5    6    7   25
CONECT    6   26   27   28
CONECT    7    8    8    8
CONECT    8    9
CONECT    9   10   29   30
CONECT   10   31   32   33
CONECT   11   12   12   13
CONECT   13   14   34
CONECT   14   15   15   16
CONECT   16   17   18
CONECT   17   35   36   37
CONECT   18   19   19
END

HMDB0014617
     RDKit          3D
Methohexital
 37 37  0  0  0  0  0  0  0  0999 V2000
   -2.4762    3.7336   -0.3479 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3956    3.1391   -0.7876 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4782    1.8105   -1.3940 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6611    0.7640   -0.6633 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8066    1.0985   -0.6149 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4116    1.2188   -1.9939 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5124    0.0176    0.0709 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0953   -0.8593    0.6494 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8353   -1.9336    1.3529 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0301   -3.1201    0.4716 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8114   -0.4802   -1.4624 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8178   -0.3617   -2.7121 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9430   -1.7557   -0.8458 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2054   -1.8870    0.5389 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3163   -3.0154    1.0557 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3372   -0.7123    1.3135 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6073   -0.8816    2.7366 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2079    0.5568    0.7077 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5730    1.5689    1.3580 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4475    4.7184    0.1064 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4292    3.2321   -0.4379 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4488    3.6323   -0.7006 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1293    1.8494   -2.4544 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5289    1.4014   -1.3944 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9556    2.0748   -0.0958 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8901    1.9538   -2.6386 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4322    0.1910   -2.4410 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4556    1.6155   -1.8916 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3280   -2.2221    2.2877 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8522   -1.5676    1.6619 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0599   -3.4982    0.5159 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3723   -3.9409    0.8268 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8104   -2.8979   -0.5935 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8339   -2.5857   -1.4779 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5777   -1.4460    2.8231 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7781    0.0846    3.2446 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8441   -1.4956    3.2262 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  5  7  1  0
  7  8  3  0
  8  9  1  0
  9 10  1  0
  4 11  1  0
 11 12  2  0
 11 13  1  0
 13 14  1  0
 14 15  2  0
 14 16  1  0
 16 17  1  0
 16 18  1  0
 18 19  2  0
 18  4  1  0
  1 20  1  0
  1 21  1  0
  2 22  1  0
  3 23  1  0
  3 24  1  0
  5 25  1  0
  6 26  1  0
  6 27  1  0
  6 28  1  0
  9 29  1  0
  9 30  1  0
 10 31  1  0
 10 32  1  0
 10 33  1  0
 13 34  1  0
 17 35  1  0
 17 36  1  0
 17 37  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
(+-)-5-Allyl-1-methyl-5-(1-methyl-2-pentynyl)barbituric acid	ChEBI
5-Allyl-1-methyl-5-(1-methyl-2-pentynyl)-2,4,6(1H,3H,5H)-pyrimidinetrione	ChEBI
5-Allyl-1-methyl-5-(1-methyl-pent-2-ynyl)-pyrimidine-2,4,6-trione	ChEBI
5-Allyl-5-(3-hexyn-2-yl)-1-methylbarbituric acid	ChEBI
alpha-DL-1-Methyl-5-allyl-5-(1'-methylpentyn-2-yl)barbituric acid	ChEBI
Methohexitalum	ChEBI
Methohexitone	ChEBI
Metohexital	ChEBI
(+-)-5-Allyl-1-methyl-5-(1-methyl-2-pentynyl)barbitate	Generator
(+-)-5-Allyl-1-methyl-5-(1-methyl-2-pentynyl)barbitic acid	Generator
5-Allyl-5-(3-hexyn-2-yl)-1-methylbarbitate	Generator
5-Allyl-5-(3-hexyn-2-yl)-1-methylbarbitic acid	Generator
a-DL-1-Methyl-5-allyl-5-(1'-methylpentyn-2-yl)barbitate	Generator
a-DL-1-Methyl-5-allyl-5-(1'-methylpentyn-2-yl)barbitic acid	Generator
alpha-DL-1-Methyl-5-allyl-5-(1'-methylpentyn-2-yl)barbitate	Generator
alpha-DL-1-Methyl-5-allyl-5-(1'-methylpentyn-2-yl)barbitic acid	Generator
Α-DL-1-methyl-5-allyl-5-(1'-methylpentyn-2-yl)barbitate	Generator
Α-DL-1-methyl-5-allyl-5-(1'-methylpentyn-2-yl)barbitic acid	Generator
Methodrexitone	HMDB
Brevital	MeSH, HMDB
Sodium, methohexital	MeSH, HMDB
Brietal	MeSH, HMDB
Lilly brand OF methohexital sodium	MeSH, HMDB
Methohexital sodium	MeSH, HMDB
Brietal-sodium	MeSH, HMDB
Brevimytal natrium	MeSH, HMDB
Jones brand OF methohexital sodium	MeSH, HMDB
Methohexital, monosodium salt	MeSH, HMDB
Monosodium salt methohexital	MeSH, HMDB
Natrium, brevimytal	MeSH, HMDB
Brietal sodium	MeSH, HMDB

Chemical Formula

C₁₄H₁₈N₂O₃

Average Molecular Weight

262.3043

Monoisotopic Molecular Weight

262.131742452

IUPAC Name

5-(hex-3-yn-2-yl)-1-methyl-5-(prop-2-en-1-yl)-1,3-diazinane-2,4,6-trione

Traditional Name

methohexital

CAS Registry Number

151-83-7

SMILES

CCC#CC(C)C1(CC=C)C(=O)NC(=O)N(C)C1=O

InChI Identifier

InChI=1S/C14H18N2O3/c1-5-7-8-10(3)14(9-6-2)11(17)15-13(19)16(4)12(14)18/h6,10H,2,5,9H2,1,3-4H3,(H,15,17,19)

InChI Key

NZXKDOXHBHYTKP-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as barbituric acid derivatives. Barbituric acid derivatives are compounds containing a perhydropyrimidine ring substituted at C-2, -4 and -6 by oxo groups.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Diazines

Sub Class

Pyrimidines and pyrimidine derivatives

Direct Parent

Barbituric acid derivatives

Alternative Parents

Substituents

Barbiturate
N-acyl urea
Ureide
1,3-diazinane
Dicarboximide
Urea
Carbonic acid derivative
Carboxylic acid derivative
Azacycle
Organic nitrogen compound
Organonitrogen compound
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Organic oxygen compound
Carbonyl group
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

barbiturates (CHEBI:102216 )
acetylenic compound (CHEBI:102216 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 31557052)

Source

Exogenous

Exogenous (PMID: 31557052)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	0.052 g/L	Not Available
LogP	1.8	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.052 g/L	ALOGPS
logP	2.43	ALOGPS
logP	2.29	ChemAxon
logS	-3.7	ALOGPS
pKa (Strongest Acidic)	8.73	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	66.48 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	71.51 m³·mol⁻¹	ChemAxon
Polarizability	27.4 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	162.588	31661259
DarkChem	[M-H]-	160.639	31661259
DeepCCS	[M+H]+	164.117	30932474
DeepCCS	[M-H]-	161.759	30932474
DeepCCS	[M-2H]-	194.644	30932474
DeepCCS	[M+Na]+	170.21	30932474
AllCCS	[M+H]+	161.7	32859911
AllCCS	[M+H-H2O]+	158.1	32859911
AllCCS	[M+NH4]+	165.0	32859911
AllCCS	[M+Na]+	166.0	32859911
AllCCS	[M-H]-	164.4	32859911
AllCCS	[M+Na-2H]-	164.8	32859911
AllCCS	[M+HCOO]-	165.3	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Methohexital	CCC#CC(C)C1(CC=C)C(=O)NC(=O)N(C)C1=O	3056.9	Standard polar	33892256
Methohexital	CCC#CC(C)C1(CC=C)C(=O)NC(=O)N(C)C1=O	1742.9	Standard non polar	33892256
Methohexital	CCC#CC(C)C1(CC=C)C(=O)NC(=O)N(C)C1=O	1919.2	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Methohexital,1TMS,isomer #1	C=CCC1(C(C)C#CCC)C(=O)N(C)C(=O)N([Si](C)(C)C)C1=O	1840.7	Semi standard non polar	33892256
Methohexital,1TMS,isomer #1	C=CCC1(C(C)C#CCC)C(=O)N(C)C(=O)N([Si](C)(C)C)C1=O	2019.1	Standard non polar	33892256
Methohexital,1TMS,isomer #1	C=CCC1(C(C)C#CCC)C(=O)N(C)C(=O)N([Si](C)(C)C)C1=O	2645.9	Standard polar	33892256
Methohexital,1TBDMS,isomer #1	C=CCC1(C(C)C#CCC)C(=O)N(C)C(=O)N([Si](C)(C)C(C)(C)C)C1=O	2071.8	Semi standard non polar	33892256
Methohexital,1TBDMS,isomer #1	C=CCC1(C(C)C#CCC)C(=O)N(C)C(=O)N([Si](C)(C)C(C)(C)C)C1=O	2253.7	Standard non polar	33892256
Methohexital,1TBDMS,isomer #1	C=CCC1(C(C)C#CCC)C(=O)N(C)C(=O)N([Si](C)(C)C(C)(C)C)C1=O	2712.7	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Methohexital GC-MS (Non-derivatized) - 70eV, Positive	splash10-001j-4390000000-8c577a429e1b4575b629	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Methohexital GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Methohexital GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Methohexital GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-0fbc-9520000000-5141cdceea7f6d5013b0	2014-09-20	Not Available	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental LC-MS/MS	LC-MS/MS Spectrum - Methohexital 35V, Positive-QTOF	splash10-00ya-3900000000-577a972e968dc27cf6a6	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methohexital 10V, Positive-QTOF	splash10-03di-2090000000-43730b3bde391b731ebe	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methohexital 20V, Positive-QTOF	splash10-00dl-3970000000-fc9a91490da8afc576f0	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methohexital 40V, Positive-QTOF	splash10-0f9x-9000000000-93587b41eae6b9864e81	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methohexital 10V, Negative-QTOF	splash10-001i-2920000000-ad50a444d0a4a9a5af2c	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methohexital 20V, Negative-QTOF	splash10-0a4l-4910000000-c5dc261173ac7024e26f	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methohexital 40V, Negative-QTOF	splash10-0006-9200000000-7cedeac5d5e1a5954aa4	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methohexital 10V, Negative-QTOF	splash10-03di-0090000000-c3de47045d3b9ea5dd1f	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methohexital 20V, Negative-QTOF	splash10-03dl-4890000000-e57232418c552e436a95	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methohexital 40V, Negative-QTOF	splash10-015c-3910000000-34338787c291ec35bb4c	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methohexital 10V, Positive-QTOF	splash10-03di-0190000000-859e807fb540e8aaf091	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methohexital 20V, Positive-QTOF	splash10-053r-0910000000-70fde9c253e18d448791	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methohexital 40V, Positive-QTOF	splash10-0udi-9300000000-67ceed0497570d0689e3	2021-09-22	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Membrane

Biospecimen Locations

Blood
Urine

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB00474	21059682	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB00474	21059682	details

Abnormal Concentrations

Not Available

Predicted Concentrations

Biospecimen	Value	Original age	Original sex	Original condition	Comments
Blood	0.000 uM	Adult (>18 years old)	Both	Normal	Predicted based on drug qualities
Blood	0.000 umol/mmol creatinine	Adult (>18 years old)	Both	Normal	Predicted based on drug qualities

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB00474

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

8683

KEGG Compound ID

C07844

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Methohexital

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

102216

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1753031

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Not Available

Enzymes

Enzyme Details

1. Gamma-aminobutyric acid receptor subunit alpha-1

General function:: Involved in ion transport
Specific function:: GABA, the major inhibitory neurotransmitter in the vertebrate brain, mediates neuronal inhibition by binding to the GABA/benzodiazepine receptor and opening an integral chloride channel
Gene Name:: GABRA1
Uniprot ID:: P14867
Molecular weight:: 51801.4

References

Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284 ]
Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423 ]
Koltchine VV, Ye Q, Finn SE, Harrison NL: Chimeric GABAA/glycine receptors: expression and barbiturate pharmacology. Neuropharmacology. 1996;35(9-10):1445-56. [PubMed:9014160 ]
Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]

Showing metabocard for Methohexital (HMDB0014617)

MOL for HMDB0014617 (Methohexital)

3D MOL for HMDB0014617 (Methohexital)

3D SDF for HMDB0014617 (Methohexital)

3D-SDF for HMDB0014617 (Methohexital)

PDB for HMDB0014617 (Methohexital)

3D PDB for HMDB0014617 (Methohexital)

SMILES for HMDB0014617 (Methohexital)

INCHI for HMDB0014617 (Methohexital)

Structure for HMDB0014617 (Methohexital)

3D Structure for HMDB0014617 (Methohexital)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

Enzymes

References